ES2308272T3 - Derivados de 1h-imidazoquinolina como inhibidores de la proteina quinasa. - Google Patents
Derivados de 1h-imidazoquinolina como inhibidores de la proteina quinasa. Download PDFInfo
- Publication number
- ES2308272T3 ES2308272T3 ES04798017T ES04798017T ES2308272T3 ES 2308272 T3 ES2308272 T3 ES 2308272T3 ES 04798017 T ES04798017 T ES 04798017T ES 04798017 T ES04798017 T ES 04798017T ES 2308272 T3 ES2308272 T3 ES 2308272T3
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- ES
- Spain
- Prior art keywords
- phenyl
- imidazo
- quinolin
- chloro
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 108090000623 proteins and genes Proteins 0.000 title description 29
- 239000003112 inhibitor Substances 0.000 title description 27
- 102000004169 proteins and genes Human genes 0.000 title description 25
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- -1 for example Chemical group 0.000 claims abstract description 246
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 102
- 125000001424 substituent group Chemical group 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 20
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- 125000002636 imidazolinyl group Chemical group 0.000 claims abstract description 17
- 125000000524 functional group Chemical group 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
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- 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 11
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US52422903P | 2003-11-21 | 2003-11-21 | |
US524229P | 2003-11-21 |
Publications (1)
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ES2308272T3 true ES2308272T3 (es) | 2008-12-01 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ES04798017T Active ES2308272T3 (es) | 2003-11-21 | 2004-11-19 | Derivados de 1h-imidazoquinolina como inhibidores de la proteina quinasa. |
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Country | Link |
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US (1) | US20080262021A1 (de) |
EP (1) | EP1687305B1 (de) |
JP (1) | JP2007511575A (de) |
KR (1) | KR20060117329A (de) |
CN (1) | CN1902200A (de) |
AT (1) | ATE400573T1 (de) |
AU (1) | AU2004295061B2 (de) |
BR (1) | BRPI0416801A (de) |
CA (1) | CA2546117A1 (de) |
DE (1) | DE602004014969D1 (de) |
ES (1) | ES2308272T3 (de) |
MX (1) | MXPA06005702A (de) |
PL (1) | PL1687305T3 (de) |
PT (1) | PT1687305E (de) |
RU (1) | RU2006121646A (de) |
WO (1) | WO2005054237A1 (de) |
Families Citing this family (100)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA05006740A (es) | 2002-12-20 | 2005-10-05 | 3M Innovative Properties Co | Imidazoquinolinas arilo-sustituidas. |
US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
AU2004268625B2 (en) | 2003-08-27 | 2011-03-31 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
EP1660026A4 (de) | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | Behandlung von cd5+ b-zell-lyphom |
WO2005079195A2 (en) | 2003-10-03 | 2005-09-01 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
AR046046A1 (es) | 2003-10-03 | 2005-11-23 | 3M Innovative Properties Co | Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas. |
KR101130928B1 (ko) | 2003-11-25 | 2012-04-12 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 치환된 이미다조 고리 시스템 및 방법 |
US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
EP1831221B1 (de) | 2004-12-30 | 2012-08-08 | 3M Innovative Properties Company | Substituierte, chirale, fusionierte 1,2 imidazo-4,5-c-ringverbindungen |
US7943609B2 (en) | 2004-12-30 | 2011-05-17 | 3M Innovative Proprerties Company | Chiral fused [1,2]imidazo[4,5-C] ring compounds |
WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
US8378102B2 (en) | 2005-02-09 | 2013-02-19 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted thiazolo[4,5-c] ring compounds and methods |
ES2475728T3 (es) | 2005-02-09 | 2014-07-11 | 3M Innovative Properties Company | Tiazoloquinolinas y tiazolonaftiridinas sustituidas con alcoxi |
AU2006216997A1 (en) | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
US7968563B2 (en) | 2005-02-11 | 2011-06-28 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
AU2006216799A1 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazonaphthyridines |
US8158794B2 (en) | 2005-02-23 | 2012-04-17 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
US8178677B2 (en) | 2005-02-23 | 2012-05-15 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
US8846710B2 (en) | 2005-02-23 | 2014-09-30 | 3M Innovative Properties Company | Method of preferentially inducing the biosynthesis of interferon |
WO2006107853A2 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
US7943636B2 (en) | 2005-04-01 | 2011-05-17 | 3M Innovative Properties Company | 1-substituted pyrazolo (3,4-C) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
WO2007030775A2 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of n-{2-[4-amino-2- (ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
KR20080083270A (ko) | 2005-11-04 | 2008-09-17 | 콜레이 파마시티컬 그룹, 인코포레이티드 | 하이드록시 및 알콕시 치환된 1에이치 이미다조퀴놀린 및방법 |
EP1988896A4 (de) | 2006-02-22 | 2011-07-27 | 3M Innovative Properties Co | Konjugate zur modifizierung von immunreaktionen |
US8329721B2 (en) | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
DK2447359T3 (en) | 2006-04-14 | 2016-02-08 | Cell Signaling Technology Inc | Genetic defects and mutated ALK kinase in human solid tumors |
US8168383B2 (en) | 2006-04-14 | 2012-05-01 | Cell Signaling Technology, Inc. | Gene defects and mutant ALK kinase in human solid tumors |
WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
WO2008030511A2 (en) | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
AU2007323820B2 (en) * | 2006-11-20 | 2012-02-23 | Novartis Ag | Salts and crystal forms of 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl] -propionitrile |
US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
EP2129379B1 (de) | 2007-02-20 | 2019-04-10 | Novartis AG | Imidazochinoline als doppellipidkinase- und mtor-hemmer |
WO2009089900A1 (en) * | 2008-01-15 | 2009-07-23 | Meda Ab | Treatment of colon diseases or prevention of colorectal carcinoma with imidazoquinoline derivatives |
CA2717948C (en) * | 2008-03-26 | 2016-09-06 | Novartis Ag | 5imidazoquinolines and pyrimidine derivatives as potent modulators of vegf-driven angiogenic processes |
PT2396307E (pt) | 2009-02-11 | 2015-02-04 | Merck Patent Gmbh | Novas carboxamidas azaheterocíclicas de amino |
CN102574845B (zh) | 2009-06-04 | 2015-09-02 | 诺华股份有限公司 | 1H-咪唑并[4,5-c]喹啉酮衍生物 |
NZ597477A (en) | 2009-06-10 | 2014-03-28 | Chugai Pharmaceutical Co Ltd | Tetracyclic compounds |
KR20120059525A (ko) | 2009-08-07 | 2012-06-08 | 메르크 파텐트 게엠베하 | 신규의 아자헤테로시클릭 화합물 |
JP5863058B2 (ja) | 2010-05-17 | 2016-02-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 1H−イミダゾ[4,5−c]キノリン |
EP3521291A1 (de) | 2010-05-20 | 2019-08-07 | Array Biopharma, Inc. | Makrocyclische verbindungen als trk-kinasehemmer |
AR084706A1 (es) * | 2010-07-16 | 2013-06-05 | Piramal Life Sciences Ltd | Derivados sustituidos de imidazoquinolinas como inhibidores de quinasa y proceso para su preparacion |
SG186199A1 (en) | 2010-07-29 | 2013-01-30 | Merck Patent Gmbh | Cyclic amine azaheterocyclic carboxamides |
UA110113C2 (xx) | 2010-07-29 | 2015-11-25 | Біциклічні азагетероциклічні карбоксаміди | |
WO2012019132A2 (en) * | 2010-08-06 | 2012-02-09 | Cell Signaling Technology, Inc. | Anaplastic lymphoma kinase in kidney cancer |
JP2013534248A (ja) | 2010-08-17 | 2013-09-02 | スリーエム イノベイティブ プロパティズ カンパニー | 脂質付加された免疫反応調節化合物の組成物、製剤及び方法 |
CN103052386B (zh) | 2010-08-20 | 2016-03-02 | 中外制药株式会社 | 含有四环化合物的组合物 |
CN103124731B (zh) * | 2010-09-16 | 2016-01-20 | 和记黄埔医药(上海)有限公司 | 稠合的杂芳基化合物及其应用 |
RU2552114C2 (ru) | 2010-09-16 | 2015-06-10 | Хатчисон Медифарма Лимитед | Конденсированные гетероарилы и их применение |
JP2014504269A (ja) * | 2010-11-05 | 2014-02-20 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー2、リミテッド | 化学化合物 |
PT2643313T (pt) | 2010-11-24 | 2016-10-11 | Merck Patent Gmbh | Quinazolina carboxamida azetidinas |
AU2011336478A1 (en) * | 2010-12-03 | 2013-06-06 | Novartis Ag | Pharmaceutical compositions |
JO3003B1 (ar) | 2011-01-14 | 2016-09-05 | Lilly Co Eli | مركب أيميدازو [4، 5 -c ] كينولين-2- واحد واستخدامه كمثبط كيناز PI3/mtor |
WO2012167088A1 (en) | 2011-06-03 | 2012-12-06 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
BR112013031039B1 (pt) | 2011-06-03 | 2020-04-28 | 3M Innovative Properties Co | compostos de hidrazino 1h-imidazoquinolina-4-aminas, conjugados feitos destes compostos, composição e composição farmacêutica compreendendo ditos compostos e conjugados, usos dos mesmos e método de fabricação do conjugado |
GB201114103D0 (en) | 2011-08-17 | 2011-09-28 | Glaxosmithkline Llc | Novel compounds |
DK2755965T3 (en) | 2011-09-12 | 2017-09-25 | Merck Patent Gmbh | PRESENT UNKNOWN IMIDAZOLAMINES AS MODULATORS OF KINASE ACTIVITY |
ES2646759T3 (es) | 2011-09-12 | 2017-12-15 | Merck Patent Gmbh | Derivados de aminopirimidina para uso como moduladores de la actividad de la quinasa |
CN103012398B (zh) * | 2011-09-19 | 2015-10-14 | 上海恒瑞医药有限公司 | 咪唑并喹啉类衍生物及其可药用盐、其制备方法及其在医药上的应用 |
PL2573073T3 (pl) * | 2011-09-26 | 2015-04-30 | Sanofi Sa | Pochodne pirazolochinolinonu, ich wytwarzanie i ich zastosowanie terapeutyczne |
JP6096205B2 (ja) | 2011-11-01 | 2017-03-15 | モッドジーン リミテッド ライアビリティ カンパニーModgene,Llc | 低減されたタンパク質キナーゼ阻害を呈するイマチニブ誘導体の使用 |
WO2013096194A1 (en) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Novel heterocyclic carboxamides as modulators of kinase activity |
HUE040055T2 (hu) | 2012-09-25 | 2019-02-28 | Chugai Pharmaceutical Co Ltd | RET inhibitor |
JP6386467B2 (ja) | 2012-11-16 | 2018-09-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | キナーゼ活性のモジュレーターとしての新規複素環式誘導体 |
AU2013344549B2 (en) | 2012-11-16 | 2018-03-08 | Xiaoling Chen | Novel imidazol-piperidinyl derivatives as modulators of kinase activity |
EA033655B1 (ru) | 2012-11-29 | 2019-11-13 | Merck Patent Gmbh | Производные азахиназолин карбоксамида |
WO2014121654A1 (zh) * | 2013-02-05 | 2014-08-14 | 山东轩竹医药科技有限公司 | 四并环激酶抑制剂 |
ES2746756T3 (es) | 2013-03-11 | 2020-03-06 | Merck Patent Gmbh | Derivados de 6-[4-(1H-imidazol-2-il)piperidin-1-il]pirimidin-4-amina como moduladores de la actividad cinasa |
WO2014177915A1 (en) * | 2013-05-01 | 2014-11-06 | Piramal Enterprises Limited | Cancer combination therapy using imidazo[4,5-c]quinoline derivatives |
WO2015022664A1 (en) * | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
WO2015022663A1 (en) * | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
US9227969B2 (en) | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
KR102410696B1 (ko) | 2014-04-03 | 2022-06-17 | 메르크 파텐트 게엠베하 | 암 치료법의 조합 |
CN106458967A (zh) | 2014-04-25 | 2017-02-22 | 中外制药株式会社 | 四环化合物的新结晶 |
CA2946518C (en) | 2014-04-25 | 2022-07-26 | Chugai Seiyaku Kabushiki Kaisha | Preparation containing tetracyclic compound at high dose |
NO2714752T3 (de) | 2014-05-08 | 2018-04-21 | ||
TWI803187B (zh) | 2014-08-08 | 2023-05-21 | 日商中外製藥股份有限公司 | 包含4環性化合物的非晶質體之固體分散體及製劑 |
EP3246047A4 (de) | 2015-01-16 | 2018-08-22 | Chugai Seiyaku Kabushiki Kaisha | Kombinationsarzneimittel |
EP3322706B1 (de) | 2015-07-16 | 2020-11-11 | Array Biopharma, Inc. | Substituierte pyrazol[1,5-a]pyridin-verbindungen als ret-kinasehemmer |
GB201516504D0 (en) | 2015-09-17 | 2015-11-04 | Astrazeneca Ab | Imadazo(4,5-c)quinolin-2-one Compounds and their use in treating cancer |
JOP20190077A1 (ar) | 2016-10-10 | 2019-04-09 | Array Biopharma Inc | مركبات بيرازولو [1، 5-a]بيريدين بها استبدال كمثبطات كيناز ret |
TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
BR112019007594A2 (pt) | 2016-10-13 | 2019-07-02 | Loyola University Of Chicago | método para bloquear a transmissão do parasita da malária |
EP3571203B1 (de) | 2017-01-18 | 2023-06-07 | Array BioPharma Inc. | Substituierte pyrazolo[1,5-a]pyrazin verbindungen als ret kinase inhibitoren |
WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
US10618896B2 (en) | 2017-08-22 | 2020-04-14 | Dynavax Technologies Corporation | Alkyl chain modified imidazoquinoline TLR7/8 agonist compounds and uses thereof |
TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
EP3710059A1 (de) | 2017-11-14 | 2020-09-23 | Dynavax Technologies Corporation | Spaltbare konjugate von tlr7/8-agonist-verbindungen, verfahren zur herstellung und verwendungen davon |
WO2019123178A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
TWI802635B (zh) | 2018-01-18 | 2023-05-21 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡咯并[2,3-d]嘧啶化合物 |
CN111615514B (zh) | 2018-01-18 | 2022-10-11 | 奥瑞生物药品公司 | 作为ret激酶抑制剂的取代的吡唑并[4,3-c]吡啶化合物 |
CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
SG11202100983XA (en) | 2018-09-04 | 2021-03-30 | Chugai Pharmaceutical Co Ltd | Method of producing tetracyclic compound |
ES2922314T3 (es) | 2018-09-10 | 2022-09-13 | Array Biopharma Inc | Compuestos heterocíclicos condensados como inhibidores de cinasa RET |
WO2022101459A1 (en) | 2020-11-16 | 2022-05-19 | Merck Patent Gmbh | Kinase inhibitor combinations for cancer treatment |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4323388A (en) * | 1980-03-10 | 1982-04-06 | Ciba-Geigy Corporation | Cyanoalkyl-phenylureas having selective herbicidal activity |
US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
US5389640A (en) * | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
JP2000119271A (ja) * | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | 1h―イミダゾピリジン誘導体 |
US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
US20040054182A1 (en) * | 2000-02-09 | 2004-03-18 | Hideo Kato | 1h-imidazopyridine derivatives |
UA74852C2 (en) * | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
MXPA05006740A (es) * | 2002-12-20 | 2005-10-05 | 3M Innovative Properties Co | Imidazoquinolinas arilo-sustituidas. |
-
2004
- 2004-11-19 AT AT04798017T patent/ATE400573T1/de not_active IP Right Cessation
- 2004-11-19 DE DE602004014969T patent/DE602004014969D1/de active Active
- 2004-11-19 MX MXPA06005702A patent/MXPA06005702A/es active IP Right Grant
- 2004-11-19 JP JP2006540347A patent/JP2007511575A/ja active Pending
- 2004-11-19 KR KR1020067009923A patent/KR20060117329A/ko not_active Application Discontinuation
- 2004-11-19 AU AU2004295061A patent/AU2004295061B2/en not_active Ceased
- 2004-11-19 ES ES04798017T patent/ES2308272T3/es active Active
- 2004-11-19 PT PT04798017T patent/PT1687305E/pt unknown
- 2004-11-19 CN CNA2004800391141A patent/CN1902200A/zh active Pending
- 2004-11-19 BR BRPI0416801-1A patent/BRPI0416801A/pt not_active IP Right Cessation
- 2004-11-19 PL PL04798017T patent/PL1687305T3/pl unknown
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- 2004-11-19 WO PCT/EP2004/013178 patent/WO2005054237A1/en active Application Filing
- 2004-11-19 CA CA002546117A patent/CA2546117A1/en not_active Abandoned
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US20080262021A1 (en) | 2008-10-23 |
PT1687305E (pt) | 2008-10-17 |
RU2006121646A (ru) | 2008-01-10 |
WO2005054237A1 (en) | 2005-06-16 |
JP2007511575A (ja) | 2007-05-10 |
CA2546117A1 (en) | 2005-06-16 |
PL1687305T3 (pl) | 2008-12-31 |
MXPA06005702A (es) | 2006-08-17 |
AU2004295061A1 (en) | 2005-06-16 |
EP1687305B1 (de) | 2008-07-09 |
CN1902200A (zh) | 2007-01-24 |
KR20060117329A (ko) | 2006-11-16 |
ATE400573T1 (de) | 2008-07-15 |
BRPI0416801A (pt) | 2007-01-09 |
DE602004014969D1 (de) | 2008-08-21 |
EP1687305A1 (de) | 2006-08-09 |
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